This year the question surrounding OVO Fest was whether Drake could top last year’s version.
Drake performing during his OVO show at the Molson Amphitheatre in Toronto, Ontario on August 4, 2014. (Peter Power for The Globe and Mail)

This year the question surrounding OVO Fest was whether Drake could top last year’s version.
Drake performing during his OVO show at the Molson Amphitheatre in Toronto, Ontario on August 4, 2014.(Peter Power for The Globe and Mail)

‘I promise you, it only gets bigger,” said one of the biggest names in pop music. “It only gets better.” The hip-hop star Drake had just completed the fifth edition of his OVO Fest, held this past weekend at Molson Canadian Amphitheatre. For the first time in its existence, the concert – a boutique version of New Jersey’s annual Summer Jam and a love letter to Toronto – covered two days. Last year’s OVO was scheduled for a pair of nights, but was cut back to a single show when day-one headliner Frank Ocean pulled out, blaming a throat injury. Nevertheless, 2013’s scaled-back affair was a doozy, thanks to the unannounced appearance of Kanye West, among many others.

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This year the question surrounding OVO Fest was whether Drake could top last year’s version. He didn’t, but he at least probably equalled it. The event’s first day was carried by a concert from Outkast, the reunited Atlanta hip-hop duo of rapper Big Boi and the sometime-actor Andre 3000. The pair exhibited no signs of friendship onstage, barely acknowledging each other as they celebrated their 20-year anniversary as a creative concern. But their horn-happy set was joyous enough, highlighted by Andre 3000’s funky 2003 hit Hey-Ya!.

Day two enjoyed the now standard cavalcade of special guests, this year including Lauryn Hill – “I guess y’all weren’t expecting me,” she surmised correctly – and Trey Songz, J. Cole, Tinashe, and the biggest names Usher and 50 Cent and the rap crew G-Unit.

Monday’s party was marked early by Hill rapping to Drake’s Draft Day and by the appearance of Drake’s mother, who arrived onstage in a wheelchair. She was a fitting starting point, naturally, for an evening presented by her son Drizzy as a sprawling retrospective musical journey of hits (including the self-mythologizing Started From the Bottom) and lesser-known introspective pieces, such as 2009’s sulking Sooner than Later, in which the state of celebrity is judged against affairs of the heart: “What good is all the cash if it doesn’t buy time, and what good is being famous if I’m never on your mind?”

Time and time again at Molson Amphitheatre, Drake promised the throng that they hadn’t seen anything yet, and that much more was to come. We should probably apply that to the man’s hyper-successful career. Aubrey Drake Graham, a half-Jewish Toronto-born former teen actor who with help from producer Noah (40) Shebib developed a brooding hip hop and R&B blend, may or may not have actually started from the bottom. That’s immaterial now, though. He’s recalibrating and ready for the next step; OVO Fest, one of North America’s most hyped hip-hop events, is now just a part of Drake’s campaign to go mogul.

His successful turn as Saturday Night Live host this winter points to a resumption of the former Degrassi: The Next Generation star’s moribund screen career. As for the business front, on Monday Drake was able to showcase a pair of artists signed to his label OVO Sound. Majid Jordan and PartyNextDoor, who made cameos, both have albums out or coming, and seek to follow the success of the Weeknd, a Toronto-based brooder who was championed early on by Drake and who is now signed to a major label.

Drake finished off OVO with an explosion of confetti and the songs Trophies and 0-100. The Grammy-winner has the former, and the latter is about his acceleration – “If I ain’t the greatest, then I’m headed for it.” For Drizzy, the foot is on the pedal, and the fast lane is his. As for bigger and better, that remains to be seen.